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Ward 8 Councilmember Marion S. Barry Jr. admitted something last week in court that came as no surprise to a lot of city residents: He’s never been very good with money.

On March 9, after being sentenced to three years of probation for not filing tax returns for five years, Barry told U.S. Magistrate Judge Deborah A. Robinson that his accounting problems and his willful disregard for tax laws can be attributed to a selfless nature. “I’m the kind of person who spends a lot of time worrying about other people and not taking care of myself financially,” said Barry.

Now he’s staring down a $246,000 combined bill from the Internal Revenue Service and the D.C. Office of Tax and Revenue. The final tab will likely be a bit lower after negotiations involving Barry’s lawyers and the tax authorities.

But District residents needn’t worry that the taxman will force the city’s only political icon into poverty. Barry still has plenty of folks ready to pass the hat and cover his mistakes, and his lawyers are busily constructing an entity to handle the contributions.

Of course, the rent party won’t be as simple as it was during his short sojourn as private citizen Barry (1999–2005). In those days, he could always count on a cadre of close buddies and old political allies to step forward and keep him solvent. And he has an impressive record of convincing influence peddlers and friends to bail him out of tight spots.

A few highlights:

In 2005, newly sworn-in Councilmember Barry collected some $35,000 at a fundraiser attended by lobbyists and business wheeler-dealers. Barry says he needed the cash to retire campaign debt. His D.C. Office of Campaign Finance (OCF) report showed that, indeed, the Barry for Ward 8 Council Committee was in the red. By $50.

In 2003, before Barry announced he would run for the council seat, a group of Barry friends gathered for a fundraiser of sorts. The Washington City Paper reported that the money wasn’t used for an exploratory committee. It went into a trust to pay his personal bills.

Just prior to his 2004 election bid, Barry twice hit up activist Sandra “SS” Seegars for a $50 loan. She complied, and in both cases he paid her back.

Now that Barry is back in office, his tin cup is getting caught in a bit of red tape. Like practically every state or local government in the United States, D.C. forbids handing government officials cash for their personal use—no matter what the motive.

Blatant attempts to influence elected D.C. officials with money are conducted in a much more civilized manner. Anyone is free to contribute to a campaign committee or a constituent-service fund. But that’s a messy avenue to winning a friend in city hall, what with the limits on contributions and requirements that donors be publicly disclosed.

Lots of Barryites have already offered to help pay his tax tab, according to Barry’s attorney Frederick Cooke. So far, Cooke and fellow Barry insider David Wilmot have had to say no thanks.

Soon enough, though, the charity will flow. In an arrangement now under consideration by Barry’s advisors, friends and associates could contribute to a bailout fund that would function as a “blind” trust. Only the trustee and the donor would know who contributed and how much. In theory, Barry would have no clue about the identity of his generous benefactors, who would—again, in theory—gain no political advantage from their generosity.

“What the campaign-finance laws are really about are about a person making some kind of gift, giving something of value, and directly or indirectly influencing [an official’s] behavior,” Cooke says. “A way that this can be avoided is to have the donor make a gift to the public official and the public official not know who it is—some sort of blind vehicle.”

Cooke’s statement is steeped in Barry history. Back in 1988, Barry’s pals requested an opinion on regulations governing a legal defense trust for then-Mayor Barry. The motivation for the fund was to defray legal costs associated with several ongoing federal probes of Barry’s conduct as mayor and of his activities not associated with the government, according to Wilmot. The OCF responded that it had no jurisdiction over a blind trust that doesn’t give funds to a candidate or a political-action committee.

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In 1990, while Barry was huddling with lawyers after his arrest on cocaine-possession charges, his legal team took the inquiry one step further. They wanted to make sure it was OK for employees of Mayor Barry to contribute to their boss’s defense fund. Again, the OCF came out on Barry’s side.

The office’s March 23, 1990, response indicates that in special circumstances, the gift restrictions don’t apply. Government employees or people doing business before the D.C. government are allowed to give nominal gifts to officials “on a special occasion such as marriage, illness or retirement,” according to city regs cited in the letter. From the OCF’s standpoint, those occasions are normally a “one-time occurrence.” The office writes that “[c]ertainly, the mayor’s unanticipated legal dilemma shares this element and may be viewed as the kind of ‘special occasion’ which similar to an illness, engenders a fellow employee’s desire to provide financial support.”

A Barry trip to the courthouse may not be so shocking now. And another interpretation will be required to determine whether his tax fiasco qualifies as a “special occasion.”

“We just have to sort of be careful and do good research and good craftsmanship….I don’t think we really need to get into the solicitation business,” says Cooke.

MICHAEL “NO SHOW” BROWN

Mayoral wannabe Michael Brown has a near-perfect record for attending mayoral forums. With a severe shortage of campaign cash, he knows that being seen and heard at public events is the cheapest way to get his message out. Send him an invite to just about any gathering of five or more people, and you can pretty much count on Brown to be there.

But his attendance record is a little spottier when it comes to the courthouse. Attorneys for D.C. Arena LP, part of Abe Pollin’s sports empire, have been trying to get Brown to shell out for his still-unpaid $636,000 tab for a luxury suite. Brown owes D.C. Arena for unpaid bills piled up by a Brown-led partnership formed to rent the suite.

Brown was supposed to appear on March 10 before D.C. Magistrate Judge Evelyn Coburn. But when LL arrived, Brown and his attorney Mark Dickson were nowhere to be seen. They never showed.

The attorney handling collections for D.C. Arena, Bruce Cherkis, requested that a bench warrant for Brown be authorized, and the court granted that request. In theory, the warrant would compel Brown to appear.

Brown referred the matter to his attorney, but Dickson did not return calls. Another lawyer, Cherylen Long, who works with Dickson, maintains that Brown “never received notice of the hearing.” Brown hasn’t budged from the position that his partners carry some responsibility for the unpaid bill. “Mr. Brown’s position is it just wasn’t his box alone and he’s not responsible for the entire amount,” says Long.

POLITICAL POTPOURRI

Barry was contrite and apologetic before Judge Magistrate Robinson at his March 9 sentencing. But by the time he walked down the steps toward a throng of reporters in front of the courthouse, Barry had returned to his playful ways. He looked straight at the bank of cameras, held his fists out in front of him, laughed, and walked toward the microphones acting as if he was wearing handcuffs. Someone in his entourage pushed his hands down. When LL commented to a Barry staffer that it appeared that Barry was playing like he was cuffed, the staffer replied, “No, man. He was just parting the Red Sea.”

Cooke was on the receiving end of another Barry joke after the sentencing. As the 15-strong Barry entourage huddled to make lunch plans, Barry shouted to Cooke: “Hey Fred, come out and have some lunch with us.” Cooke smiled and replied that he was heading back to the office. “I have just a little bit of legal work to do,” he said. Barry retorted, “It’s OK—I’ll take you off the clock.” Both lawyer and client laughed heartily. Cooke has never been “on the clock” with Barry. His defense efforts are provided on a pro-bono basis.

D.C. Council Chairman Linda Cropp seems to be taking a page out of Daniel Snyder’s business plan when it comes to raising campaign cash for her mayoral bid. After bringing home an impressive $500,000 in 38 days, Cropp snagged the most sought-after free-agent fundraiser on the market: Max Berry, who’s been courted by all the mayoral candidates, says he’ll serve as Cropp’s co-chairman for finance. His A-list of wealthy donors is highly coveted by politicians around town, but Berry, 70, has been sticking to charity work since the end of the 2002 election cycle. Bringing in the globe-trotting international lawyer won’t do much to shake Cropp’s reputation as the establishment candidate. Her newest recruit’s fundraising prowess dates back to D.C.’s very first citywide election, when the Rev. Walter Fauntroy won the 1971 race for nonvoting D.C. Delegate to Congress. Berry also served as finance chair for Barry’s first and second mayoral elections and got behind the relatively unknown Anthony A. Williams back in 1998. Cropp’s chief rival, Ward 4 Councilmember Adrian Fenty, only recently gave up on wooing Berry. And the lobbying from Fenty ran right up to the moment he signed on with Cropp. “I exchanged six phone calls with him,” says Berry.

—James Jones

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